diff --git a/test/images/Makefile b/test/images/Makefile
index deca1cd2b67..c653f87f8c0 100644
--- a/test/images/Makefile
+++ b/test/images/Makefile
@@ -14,6 +14,7 @@
 
 REGISTRY ?= gcr.io/kubernetes-e2e-test-images
 GOARM ?= 7
+DOCKER_CERT_BASE_PATH ?=
 QEMUVERSION=v2.9.1
 GOLANG_VERSION=1.13.9
 export
diff --git a/test/images/agnhost/OWNERS b/test/images/agnhost/OWNERS
new file mode 100644
index 00000000000..83a3a4d90cc
--- /dev/null
+++ b/test/images/agnhost/OWNERS
@@ -0,0 +1,2 @@
+approvers:
+  - claudiubelu
diff --git a/test/images/agnhost/README.md b/test/images/agnhost/README.md
index d929fd3022a..bc630551f71 100644
--- a/test/images/agnhost/README.md
+++ b/test/images/agnhost/README.md
@@ -40,7 +40,7 @@ For example, let's consider the following `pod.yaml` file:
       containers:
       - args:
         - dns-suffix
-        image: us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11
+        image: us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14
         name: agnhost
       dnsConfig:
         nameservers:
@@ -207,7 +207,7 @@ Usage:
 
 ```console
 guestbook="test/e2e/testing-manifests/guestbook"
-sed_expr="s|{{.AgnhostImage}}|us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11|"
+sed_expr="s|{{.AgnhostImage}}|us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14|"
 
 # create the services.
 kubectl create -f ${guestbook}/frontend-service.yaml
@@ -290,14 +290,14 @@ Examples:
 
 ```console
 docker run -i \
-  us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11 \
+  us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14 \
   logs-generator --log-lines-total 10 --run-duration 1s
 ```
 
 ```console
 kubectl run logs-generator \
   --generator=run-pod/v1 \
-  --image=us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11 \
+  --image=us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14 \
   --restart=Never \
   -- logs-generator -t 10 -d 1s
 ```
@@ -464,7 +464,7 @@ Usage:
 ```console
     kubectl run test-agnhost \
       --generator=run-pod/v1 \
-      --image=us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11 \
+      --image=us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14 \
       --restart=Never \
       --env "POD_IP=<POD_IP>" \
       --env "NODE_IP=<NODE_IP>" \
@@ -519,7 +519,7 @@ Usage:
 ```console
     kubectl run test-agnhost \
       --generator=run-pod/v1 \
-      --image=us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11 \
+      --image=us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14 \
       --restart=Never \
       --env "BIND_ADDRESS=localhost" \
       --env "BIND_PORT=8080" \
@@ -647,6 +647,6 @@ The Windows `agnhost` image includes a `nc` binary that is 100% compliant with i
 
 ## Image
 
-The image can be found at `us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.11` for both Linux and
+The image can be found at `us.gcr.io/k8s-artifacts-prod/e2e-test-images/agnhost:2.14` for both Linux and
 Windows containers (based on `mcr.microsoft.com/windows/servercore:ltsc2019`,
 `mcr.microsoft.com/windows/servercore:1903`, and `mcr.microsoft.com/windows/servercore:1909`).
diff --git a/test/images/agnhost/VERSION b/test/images/agnhost/VERSION
index ae656d47364..123a39a8e91 100644
--- a/test/images/agnhost/VERSION
+++ b/test/images/agnhost/VERSION
@@ -1 +1 @@
-2.13
+2.14
diff --git a/test/images/agnhost/agnhost.go b/test/images/agnhost/agnhost.go
index c8436aacd4a..ade9f23c1e8 100644
--- a/test/images/agnhost/agnhost.go
+++ b/test/images/agnhost/agnhost.go
@@ -49,7 +49,7 @@ import (
 )
 
 func main() {
-	rootCmd := &cobra.Command{Use: "app", Version: "2.13"}
+	rootCmd := &cobra.Command{Use: "app", Version: "2.14"}
 
 	rootCmd.AddCommand(auditproxy.CmdAuditProxy)
 	rootCmd.AddCommand(connect.CmdConnect)
diff --git a/test/images/busybox/OWNERS b/test/images/busybox/OWNERS
new file mode 100644
index 00000000000..83a3a4d90cc
--- /dev/null
+++ b/test/images/busybox/OWNERS
@@ -0,0 +1,2 @@
+approvers:
+  - claudiubelu
diff --git a/test/images/cloudbuild.yaml b/test/images/cloudbuild.yaml
index 2912b934601..0408b7e891b 100644
--- a/test/images/cloudbuild.yaml
+++ b/test/images/cloudbuild.yaml
@@ -7,6 +7,7 @@ timeout: 5400s
 # or any new substitutions added in the future.
 options:
   substitution_option: ALLOW_LOOSE
+  machineType: 'N1_HIGHCPU_8'
 steps:
   - name: 'gcr.io/k8s-testimages/gcb-docker-gcloud:v20190906-745fed4'
     entrypoint: make
@@ -17,6 +18,10 @@ steps:
     - BASE_REF=$_PULL_BASE_REF
     - WHAT=$_WHAT
     - REGISTRY=gcr.io/k8s-staging-e2e-test-images
+    - DOCKER_CERT_BASE_PATH=/root
+    - REMOTE_DOCKER_URL_1809=tcp://img-promoter-1809.eastus.cloudapp.azure.com:2376
+    - REMOTE_DOCKER_URL_1903=tcp://img-promoter-1903.eastus.cloudapp.azure.com:2376
+    - REMOTE_DOCKER_URL_1909=tcp://img-promoter-1909.eastus.cloudapp.azure.com:2376
     # TODO(claudiub): Readd the REMOTE_DOCKER_URL_${os_version} to reenable the Windows test image building process.
     args:
     - all-build-and-push
diff --git a/test/images/image-util.sh b/test/images/image-util.sh
index cd4b929692d..a027cec8c75 100755
--- a/test/images/image-util.sh
+++ b/test/images/image-util.sh
@@ -21,6 +21,11 @@ set -o pipefail
 TASK=$1
 WHAT=$2
 
+# Connecting to a Remote Docker requires certificates for authentication, which can be found
+# at this path. By default, they can be found in the ${HOME} folder. We're expecting to find
+# here ".docker-${os_version}" folders which contains the necessary certificates.
+DOCKER_CERT_BASE_PATH="${DOCKER_CERT_BASE_PATH:-${HOME}}"
+
 KUBE_ROOT="$(cd "$(dirname "${BASH_SOURCE[0]}")/../.." && pwd -P)"
 source "${KUBE_ROOT}/hack/lib/logging.sh"
 source "${KUBE_ROOT}/hack/lib/util.sh"
@@ -135,8 +140,8 @@ build() {
       # The node requires TLS authentication, and thus it is expected that the
       # ca.pem, cert.pem, key.pem files can be found in the ${HOME}/.docker-${os_version} folder.
       # TODO(claudiub): add "build --isolation=hyperv" once GCE introduces Hyper-V support.
-      docker --tlsverify --tlscacert "${HOME}/.docker-${os_version}/ca.pem" \
-        --tlscert "${HOME}/.docker-${os_version}/cert.pem" --tlskey "${HOME}/.docker-${os_version}/key.pem" \
+      docker --tlsverify --tlscacert "${DOCKER_CERT_BASE_PATH}/.docker-${os_version}/ca.pem" \
+        --tlscert "${DOCKER_CERT_BASE_PATH}/.docker-${os_version}/cert.pem" --tlskey "${DOCKER_CERT_BASE_PATH}/.docker-${os_version}/key.pem" \
         -H "${REMOTE_DOCKER_URL}" build --pull -t "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}-${os_version}" \
         --build-arg BASEIMAGE="${BASEIMAGE}" -f $dockerfile_name .
     else
@@ -192,21 +197,16 @@ push() {
       docker push "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}"
     elif [[ -n "${REMOTE_DOCKER_URL:-}" ]]; then
       # NOTE(claudiub): We're pushing the image we built on the remote Windows node.
-      docker --tlsverify --tlscacert "${HOME}/.docker-${os_version}/ca.pem" \
-        --tlscert "${HOME}/.docker-${os_version}/cert.pem" --tlskey "${HOME}/.docker-${os_version}/key.pem" \
+      docker --tlsverify --tlscacert "${DOCKER_CERT_BASE_PATH}/.docker-${os_version}/ca.pem" \
+        --tlscert "${DOCKER_CERT_BASE_PATH}/.docker-${os_version}/cert.pem" --tlskey "${DOCKER_CERT_BASE_PATH}/.docker-${os_version}/key.pem" \
         -H "${REMOTE_DOCKER_URL}" push "${REGISTRY}/${image}:${TAG}-${os_name}-${arch}-${os_version}"
     else
       echo "Cannot push the image '${image}' for ${os_arch}. REMOTE_DOCKER_URL_${os_version} should be set, containing the URL to a Windows docker daemon."
+      # we should exclude this image from the manifest list as well, we couldn't build / push it.
+      os_archs=$(printf "%s\n" "$os_archs" | grep -v "$os_arch" || true)
     fi
   done
 
-  # NOTE(claudiub): if the REMOTE_DOCKER_URL var is not set, or it is an empty string, we mustn't include
-  # Windows images into the manifest list.
-  if test -z "${REMOTE_DOCKER_URL:-}" && printf "%s\n" "$os_archs" | grep -q '^windows'; then
-    echo "Skipping pushing the image '${image}' for Windows. REMOTE_DOCKER_URL_\${os_version} should be set, containing the URL to a Windows docker daemon."
-    os_archs=$(printf "%s\n" "$os_archs" | grep -v "^windows" || true)
-  fi
-
   if test -z "${os_archs}"; then
     # this can happen for Windows-only images if they have been skipped entirely.
     echo "No image for the manifest list. Skipping ${image}."
diff --git a/test/images/kitten/BASEIMAGE b/test/images/kitten/BASEIMAGE
index 4a0492bdfce..ca4cc5610bf 100644
--- a/test/images/kitten/BASEIMAGE
+++ b/test/images/kitten/BASEIMAGE
@@ -1,5 +1,8 @@
-linux/amd64=REGISTRY/agnhost:2.13-linux-amd64
-linux/arm=REGISTRY/agnhost:2.13-linux-arm
-linux/arm64=REGISTRY/agnhost:2.13-linux-arm64
-linux/ppc64le=REGISTRY/agnhost:2.13-linux-ppc64le
-linux/s390x=REGISTRY/agnhost:2.13-linux-s390x
+linux/amd64=REGISTRY/agnhost:2.14-linux-amd64
+linux/arm=REGISTRY/agnhost:2.14-linux-arm
+linux/arm64=REGISTRY/agnhost:2.14-linux-arm64
+linux/ppc64le=REGISTRY/agnhost:2.14-linux-ppc64le
+linux/s390x=REGISTRY/agnhost:2.14-linux-s390x
+windows/amd64/1809=REGISTRY/agnhost:2.14-windows-amd64-1809
+windows/amd64/1903=REGISTRY/agnhost:2.14-windows-amd64-1903
+windows/amd64/1909=REGISTRY/agnhost:2.14-windows-amd64-1909
diff --git a/test/images/kitten/Dockerfile b/test/images/kitten/Dockerfile
index 48d6f860d88..f92dd7a89d4 100644
--- a/test/images/kitten/Dockerfile
+++ b/test/images/kitten/Dockerfile
@@ -16,3 +16,4 @@ ARG BASEIMAGE
 FROM $BASEIMAGE
 COPY html/kitten.jpg kitten.jpg
 COPY html/data.json data.json
+CMD ["test-webserver"]
diff --git a/test/images/kitten/OWNERS b/test/images/kitten/OWNERS
new file mode 100644
index 00000000000..a31515e32b5
--- /dev/null
+++ b/test/images/kitten/OWNERS
@@ -0,0 +1,3 @@
+approvers:
+  - claudiubelu
+  - mkumatag
diff --git a/test/images/nautilus/BASEIMAGE b/test/images/nautilus/BASEIMAGE
index 4a0492bdfce..ca4cc5610bf 100644
--- a/test/images/nautilus/BASEIMAGE
+++ b/test/images/nautilus/BASEIMAGE
@@ -1,5 +1,8 @@
-linux/amd64=REGISTRY/agnhost:2.13-linux-amd64
-linux/arm=REGISTRY/agnhost:2.13-linux-arm
-linux/arm64=REGISTRY/agnhost:2.13-linux-arm64
-linux/ppc64le=REGISTRY/agnhost:2.13-linux-ppc64le
-linux/s390x=REGISTRY/agnhost:2.13-linux-s390x
+linux/amd64=REGISTRY/agnhost:2.14-linux-amd64
+linux/arm=REGISTRY/agnhost:2.14-linux-arm
+linux/arm64=REGISTRY/agnhost:2.14-linux-arm64
+linux/ppc64le=REGISTRY/agnhost:2.14-linux-ppc64le
+linux/s390x=REGISTRY/agnhost:2.14-linux-s390x
+windows/amd64/1809=REGISTRY/agnhost:2.14-windows-amd64-1809
+windows/amd64/1903=REGISTRY/agnhost:2.14-windows-amd64-1903
+windows/amd64/1909=REGISTRY/agnhost:2.14-windows-amd64-1909
diff --git a/test/images/nautilus/Dockerfile b/test/images/nautilus/Dockerfile
index c344116bf8c..2cb4784a8fa 100644
--- a/test/images/nautilus/Dockerfile
+++ b/test/images/nautilus/Dockerfile
@@ -16,3 +16,4 @@ ARG BASEIMAGE
 FROM $BASEIMAGE
 COPY html/nautilus.jpg nautilus.jpg
 COPY html/data.json data.json
+CMD ["test-webserver"]
diff --git a/test/images/nautilus/OWNERS b/test/images/nautilus/OWNERS
new file mode 100644
index 00000000000..a31515e32b5
--- /dev/null
+++ b/test/images/nautilus/OWNERS
@@ -0,0 +1,3 @@
+approvers:
+  - claudiubelu
+  - mkumatag